


A Surprise

by sixtysevenlmpala



Category: Supernatural
Genre: Batcave, Crossdressing, Crossdressing Kink, Crossdressing!Dean, Drunk Sex, Drunkenness, Fluff, Halloween, Halloween Costumes, Happy Sex, Holidays, M/M
Language: English
Status: Completed
Published: 2013-11-02
Updated: 2013-11-02
Packaged: 2017-12-31 05:27:06
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,390
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1027754
Author URL: https://archiveofourown.org/users/sixtysevenlmpala/pseuds/sixtysevenlmpala
Summary: <blockquote class="userstuff">
              <p>Leaning against the doorframe with one hip cocked out and playful bedroom eyes flashing at Sam is his brother, decked out in an honest-to-God <a href="http://i01.i.aliimg.com/wsphoto/v0/1116993963/Free-Shipping-4-Pieces-Womens-Sexy-French-Maid-Lace-Corset-Costume-Dresses-Halloween-Costumes-Cosplay.jpg">maid’s outfit</a>, complete with a dainty little feather duster dangling from his thick fingers and a satin ribbon tied in a bow around his neck.</p>
<p>“Get it? ‘Cause I do all the fuckin’ chores around here.” Dean throws his head back in laughter.</p>
            </blockquote>





	A Surprise

**Author's Note:**

> A day late, but happy Halloween! Have some happy Winchesters having drunken costume-themed sex. You are welcome.

“Hey, Sammy,” Dean’s voice calls from down the hall, “ _Sammy_ ,” followed by a giggle that echoes down the halls of the Batcave. Dean’s not exactly the giggling type, but by Sam’s count he’s currently got four glasses of whiskey, a good few bottles of beer _and_ two tons of chocolate sloshing around inside of him, and that changes things.

Sam loves when Dean’s a happy drunk. He’s all laughs and sloppy kisses and clumsy grabby hands everywhere. It doesn’t happen often: this time, it probably has something to do with the fact that it’s Halloween, Dean’s favourite holiday ever.

More giggling. “Sam! Get in here. Got a surprise.”

Sam rolls his eyes affectionately and gets up from his chair, wobbling a little on his feet – okay, so maybe he’s matched Dean for every drink so far, but whatever – and follows the sound of Dean’s voice to Dean’s room, where Sam freezes open-mouthed on the spot. Because leaning against the doorframe with one hip cocked out and playful bedroom eyes flashing at Sam is his brother, decked out in an honest-to-God [maid’s outfit](http://i01.i.aliimg.com/wsphoto/v0/1116993963/Free-Shipping-4-Pieces-Womens-Sexy-French-Maid-Lace-Corset-Costume-Dresses-Halloween-Costumes-Cosplay.jpg), complete with a dainty little feather duster dangling from his thick fingers and a satin ribbon tied in a bow around his neck.

“Get it? ‘Cause I do all the fuckin’ chores around here.” Dean throws his head back in laughter.

Sam swallows, staring. “Jesus Christ.”

Leaning in close so his breath tickles Sam’s neck, Dean mutters, “I prefer Dean.” Then he laughs again, pushes away from Sam and flounces over to his bed – ‘flouncing’ being the best adjective for how he moves, multiple layers of skirts angling out from his waist and swishing around his thighs – flopping onto the mattress.

“Right,” Sam smiles, following him slowly, ending up standing by the bed and looking down at him.

The bodice is sheer lace, Dean’s muscles softly defined through it, and the way the skirt juts outwards fashions hips he doesn’t usually have. It’s short, though, just barely covering what it needs to, white underskirts gathered around his thighs and probably scratching lightly at his skin. Sam knows how sensitive his inner thighs are. His eyes follow the stretch of Dean’s legs, and he’s wearing _holdups_ , white frills around the tops and black fishnet hugging the soft, muscular curve of his legs. And—God, those are definitely _not_ Dean’s old boots or his slippers on his feet—those are sleek black heels, women’s heels, fitting effortlessly onto Dean’s feet.

Yeah, Jesus _Christ_.

“Seein’ somethin’ you like, Sammy?” Dean drawls, but he’s grinning idiotically and the tone of his voice clearly says he’s joking. He probably thinks this is the funniest thing he’s ever done, but Sam can already feel his cock stirring in his sweatpants.

“I— uh.” Sam blinks a few times, mouth dry, and Dean reaches out, catches his hand and tugs so that he falls clumsily onto the bed.

“Think I look hot, baby?” Dean slurs. “Like a sexy French maid, huh?” His hand is raking through Sam’s hair, making it crazy and mussed, and he’s laughing, letting his head fall back against the bed and exposing his throat. There’s fluffy white feathers around the bow.

Without thinking about it too much – just enough that his cheeks are burning a little with the vague notion that Dean might tease the shit out of him for this – Sam dives down and kisses Dean hard and forceful, teeth clicking a little as he shoves his tongue into Dean’s lax mouth. His hands wander down the side of Dean’s neck, tracing the ribbon before skating down to his waist, and Sam’s breath catches at the feel of the lace beneath his fingers.

Dean pulls back to look him in the eye, struggling to focus on something so close. “Hey, wow, seriously?” he asks, and Sam flushes further.

“You look good,” he mumbles by way of explanation.

He bites at Dean’s neck, lips brushing the band of satin, and Dean laughs breathlessly, hand tightening in Sam’s hair. “You like me dressin’ up for you, Sammy?” he whispers, and Sam pants open mouthed against his neck. “This make you hard?”

“ _God_. Yes,” Sam grits out, grinding his cock into Dean’s thigh through his sweatpants for emphasis, and Dean giggles, turns it into a moan as soon as Sam lays a hand on his thigh, slowly sliding his palm upwards until he reaches Dean’s cock.

Which, Sam discovers, is concealed underneath a material way too silky to be boxers. “Came with the outfit,” Dean tells him, dirty grin as he pushes at Sam’s chest to get him to back off, then gathers up the skirts in his hands and pulls them upwards, exposing black satin panties with white frills of lace around the edges, his cock a noticeable bulge underneath.

“Fucking hell, Dean,” Sam growls, and then he’s _on_ him, big hands spreading him wider as he bites sloppily at his inner thigh, listening to Dean’s gasps climbing higher and higher as Sam trails his mouth towards that inviting package.

“Sammy,” Dean whines, squirming as Sam lets his breath wash out over the panties. His hands are fisted in the skirt, holding it tight and out of the way as he stares down with blown pupils at Sam between his legs. Sam chuckles and lays his mouth over what must be the head of Dean’s cock, a wet, open-mouthed kiss through the silky fabric, and Dean curses, cock twitching. Settling in, Sam drags the flat of his tongue over the ridge of Dean’s cock, does it again and again because he likes the noises Dean’s making and the smoothness under his tongue, fingers toying with the edges of the holdups.

“Gonna taste you,” Sam mutters, hauling Dean closer to his mouth by his thighs, yanking the panties aside and exposing his hole, “lick you open like the slut you’re dressed like,” and he can _see_ Dean clench up, muscles fluttering in anticipation. Sam really can’t resist that kind of invitation. He dives in, alcohol fuelling the enthusiasm he already has for eating Dean out. Spreads him open with both thumbs, doesn’t waste any time, spears his tongue deep and tastes every inch of him that he can. Dean’s so lax that he just opens right up, melting under Sam’s hands and grinding onto his face, moaning when Sam pulls back to trace around his rim before plunging back inside, never leaving a chance for Dean to breathe.

 “Fuck me, God, fuck me,” Dean mutters, hand tugging insistently at Sam’s hair. “C’mon, Sam, fuck. You better get your cock in me right fuckin’ now, or I swear to god I’ll punch you, skirt or no skirt.”

Sam laughs, “Later. Such a slut,” and Dean shudders at the word. Sam raises an eyebrow. “You like when I call you that?”

“Shut up,” Dean shoots back, voice breathy, and Sam grins.

An idea occurs to Sam, and he pulls away – much to Dean’s aggravation – flops lengthways beside him and then grabs for Dean’s thighs, manhandling him until he’s straddling Sam. “C’mon,” Sam mutters, hauling Dean closer so he’s got a knee either side of Sam’s neck, gazing down at him with lidded eyes. “Ride me,” Sam growls, “ride my face, then, you want something in your ass so bad, c’mon,” and Dean whimpers, shuffles up so he’s hovering over Sam’s mouth, and Sam just tugs him down, sits him right there on his face and thrusts his tongue into his body as he holds the panties out of the way.

Dean’s shuddering above him, holding the dress up with one hand and bracing himself on the headboard with the other. He’s goddamn beautiful, head tipped back and chest heaving in his pretty little outfit, hips undulating as he rocks down onto Sam’s mouth. Sam smiles against him and laps at his hole, suckling at his tight balls through the satin before curling his tongue inside of him, accompanying it with two long fingers sliding smoothly into his body.

“ _Sam_ ,” Dean gasps out, shivering and bearing down eagerly onto Sam’s fingers. “Yeah, more. Now.”

Sam fingers him hard and relentless, Dean’s desperate grunts making his own cock twitch in his sweatpants, crooks his fingers and spreads them to lick in between until Dean’s clutching at his hair, yanking painfully.

“Come _on_ ,” Dean demands, “want your goddamn cock inside me,” and Sam groans himself, pushing up with his hands ‘til Dean gets the message and sits up. Sam grins up at him, running his hands up and down Dean’s sides, appreciating the view.

“You want me to fuck you?” Sam asks, voice low.

“Yes.”

“Nice an’ slow, get you all slick an’ just ease on in there?” Sam licks his lips. “Or, no, you don’t want it like that, do you? You wanna _feel_ it,” he says, squeezing Dean’s ass cheeks. “Want my dick to split you open, huh, want me to shove you down an’ use you.”

“Sam,” Dean mutters, warning him and urging him on all at once, and Sam tips him over easily, letting him fall to the bed beside him and following him over. Sam gets between Dean’s legs and spreads them, pushes his knees up to his chest, and Dean moves to take the panties off. Sam lets him, but when Dean’s hands go for the holdups, he stops him, closes his fingers tight around his wrist.

“No,” Sam breathes, kissing him deep and messy, “keep ‘em on. Want you to keep all the rest of it on.”

Sam grabs the lube from the bedside table and shucks his sweatpants off, slicking up his hard cock and giving Dean a quick prep, brief because he knows what Dean wants.

“Y’know how sluts get fucked, Dean,” Sam grins, face inches from Dean’s, teasing the head of his cock over his hole.

“On their backs with their fuckin’ heels in the air,” Dean grunts, and Sam laughs darkly, slings Dean’s legs over his shoulders and slides home in one quick thrust, Dean throwing his head back and arching into it, tendons in his neck standing out starkly as he grits his teeth against a moan. “Yeah, Sam, like that—fuck.”

Dean’s eyes are closed, but that’s okay, ‘cause Sam’s staring enough for the both of them, drinking in every little inch of Dean; bare cock brushing up against the inner skirts of his costume, leaving trails of precome clinging to the netting; pale thighs clashing with the sheer black holdups. The band around his neck has shifted a little with the sweat, bow not quite central any more, and Sam leans down to taste the salt, shoving deeper as he does, making Dean gasp. “You’re so fuckin’ hot,” Sam pants, snapping his hips, “in your little outfit.”

Dean giggles again, and that has his muscles quivering around Sam’s cock so he growls and fucks him harder, shoving little gasps out of his mouth. Dean spreads his legs wider, slipping off Sam’s shoulders, but Sam holds him open in a wide ‘v’ shape, sharp heels pointed straight at the ceiling as Sam drives his cock into his body again and again.

“Why’d you really choose the maid?” Sam breathes, slurring his words a little, and Dean whimpers. “Was it ‘cause you like the idea of that, huh? You here, cleaning all day, just waiting for the master of the house to come home an’ fuck you senseless.” Dean moans, and Sam laughs, straightening up so his hands can wander freely over the outfit. “Could spread you over every surface of this place, couldn’t I,” he goes on, punctuating every other word with a hard thrust. “Everywhere you fuckin’ cleaned, we’d just make it _dirty_ again,” and Dean tightens around Sam’s cock, writhing on the bed.

“Yeah,” he whispers, barely a fraction of a sound, but Sam hears it and smirks.

“Maybe one day I’ll make you put it on, get my cock out an’ watch you flicking that goddamn duster around,” he breathes, “no panties, though – wanna see that perfect ass every time you bend over.”

“ _Sam_ ,” Dean gasps, and Sam fucks into him rough and ruthless, and Dean’s gasping and tilting his hips to get him deeper and tugging restlessly at the skirts of his outfit, and all of a sudden his whole body’s seizing up and he’s coming all over himself, drops landing on the netted underskirt, shooting onto the smooth black bodice.

“Oh fuck, Jesus Christ,” Sam grits out, mouth dropping open as he slams forward and spills inside Dean, filling him up with come and fucking it right out of him, messy and slick. Dean shivers at the feeling, goosebumps rising all over his exposed skin, but he just lies back and takes it, hands coming up to stroke through Sam’s hair as he trembles through the aftershocks and slumps over Dean, fabric crinkling beneath his spent body.

Neither of them say a word for a while, but eventually Dean grunts out, “Get your lard-ass off’a me,” and Sam breaks into a bout of snickers against his neck.

“You’re the one who’s been eating all the candy in the state, Dean,” he laughs, patting Dean’s slightly bulged out belly as he rolls off of him.

Dean thwacks him in the shoulder. “Fuck you.”

“Fuck _you_ , actually,” Sam laughs, reaching over and pulling Dean in for a kiss. Dean returns it, both of them sloppy and uncoordinated and hazy, tongues slow and sleepy, lips sliding together until Sam tugs Dean on top of him and breaks the contact. “You really do look pretty, y’know.”

Dean flushes a dark red and shifts uncomfortably, but Sam’s hands on his hips hold him still until he relaxes. “Whatever.” Sam smiles up at him, tip of his tongue peeking through his teeth as his fingers trace the neckline of the dress, and Dean lets out a giggle.

“What?” Sam asks, amused.

“You really got off on this.”

Sam shrugs, muscles fluid, veins buzzing. “Uh-huh.”

Dean lets out another drunken giggle. “So did I.”

“Yeah, you did,” Sam says.

A pause. “So, we’re keepin’ this thing, right?”

Sam grins, delighted. “You bet your goddamn ass,” he says, with a playful spank to the aforementioned ass.

Dean bites his lip, lets a slow smile spread across his face. “Well, happy fuckin’ Halloween,” he murmurs, and Sam laughs in agreement.

**Author's Note:**

> Thanks for reading, feel free to leave a comment/kudos if you liked! :-)


End file.
